[ CAS No. 123696-02-6 ]

Name: 123696-02-6|3-Chloro-5-methoxypyridazine|97%
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Quality Control of [ 123696-02-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 123696-02-6 ]

CAS No. :	123696-02-6	MDL No. :	MFCD08236839
Formula :	C₅H₅ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XLGRINRFBNCHQS-UHFFFAOYSA-N
M.W :	144.56	Pubchem ID :	10975612
Synonyms :

Calculated chemistry of [ 123696-02-6 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	33.53
TPSA :	35.01 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.73
Log Po/w (XLOGP3) :	0.78
Log Po/w (WLOGP) :	1.14
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	1.56
Consensus Log Po/w :	1.11

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.65
Solubility :	3.2 mg/ml ; 0.0221 mol/l
Class :	Very soluble
Log S (Ali) :	-1.1
Solubility :	11.6 mg/ml ; 0.0802 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.37
Solubility :	0.612 mg/ml ; 0.00424 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 123696-02-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 123696-02-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 123696-02-6 ]
Downstream synthetic route of [ 123696-02-6 ]

[ 123696-02-6 ] Synthesis Path-Upstream 1~10

1
[ 123696-02-6 ]
[ 20733-11-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4716 - 4730

2
[ 67-56-1 ]
[ 123696-02-6 ]
[ 2096-20-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1473 - 1476

3
[ 123696-01-5 ]
[ 123696-02-6 ]

Yield	Reaction Conditions	Operation in experiment
45%	at 1100℃; for 0.166667 h;	A suspension of 5-methoxypyridazin-3(2H)-one (250 mg, 1.98 mmol) in phosphorus oxychloride (1.5 mL, 16 mmol) was stirred at 100C for 10 minutes. The reaction mixture was poured into ice water and sodium carbonate was added until a basic pH-was reached. The mixture was extracted with diethyl ether, the organic phase was dried (magnesium sulfate), filtered and the solvent was removed in vacuum. The residue was crystallized from 1,2-dichloroethane to give 130 mg (45 percent yield) of the title compound. LC-MS (Method 5): R = 0.85 mm; MS (ESIpos): m/z = 145 [M+H] 1H-NMR (400 MHz, DMSO-d6) [ppm]: 2.495 (0.78), 2.499 (1.07), 2.503 (0.84), 3.317 (11.94),3.944 (16.00), 7.528 (2.28), 7.534 (2.29), 8.988 (2.34), 8.994 (2.34).

Reference： [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1473 - 1476
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4716 - 4730
[3] Monatshefte fuer Chemie, 1989, vol. 120, p. 329 - 342
[4] Patent: WO2017/102091, 2017, A1, . Location in patent: Page/Page column 455; 456

4
[ 7732-18-5 ]
[ 123696-02-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide; trichlorophosphate In hexane; dichloromethane; ethyl acetate	E. 3-Hydroxy-5-methoxypyridazine (629.6 g, 4.99 moles) and phosphorus oxychloride (2.5 L, 27 moles) were added to a 5 L round bottomed flask equipped with a heating mantle and a mechanical stirrer. The resulting stirred slurry was rapidly heated (<30 min) to 75° C. At this temperature the heating mantle was removed. The reaction mixture continued to exotherm to a final temperature of 82.3° C. After the solids had dissolved in the darkening reaction mixture, stirring was continued an additional 2 minutes. The homogeneous reaction mixture was then rapidly cooled to room temperature with an ice/water bath. The reaction mixture was concentrated via rotary evaporator using pump vacuum and a water bath temperature of 45° C. The residue was taken up in 2 L of CH₂ Cl₂ and slowly poured into a stirring mixture of 2 L CH₂ Cl₂ and 6 L of H₂ O chilled to 10° C. The layers were separated and enough 50percent NaOH was added to the aqueous phase to give a pH of 2-4. The aqueous phase was extracted with additional CH₂ Cl₂ (2*2 L). The combined organic layers were washed with 4 L of H₂ O and dried (MgSO₄). The solution was vacuum filtered through 1 kg of silica gel. The silica gel was washed with 4 L of ethyl acetate/hexane (1:1). The filtrate was concentrated in vacuo to afford 564 g (78percent yield) of 3-chloro-5-methoxypyridazine as a pale yellow solid. The product was stored in a freezer to prevent gradual decomposition. The product was recrystallized from ethyl acetate/cyclohexane to give a white solid, mp=98°-100° C. Anal. Calc. for C₅ H₅ N₂ OCl: C, 41.54; H, 3.49; N, 19.38 Found: C, 41.62; H, 3.51; N, 19.34
78%	With sodium hydroxide; trichlorophosphate In dichloromethane; ethyl acetate	E. 3-Hydroxy-5-methoxypyridazine (629.6 g, 4.99 moles) and phosphorous oxychloride (2.5 L, 27 moles) were added to a 5 L round bottomed flask equipped with a heating mantle and a mechanical stirrer. The resulting stirred slurry was rapidly heated (<30 min) to 75° C. At this temperature the heating mantle was removed. The reaction mixture continued to exotherm to a final temperature of 82.3° C. After the solids had dissolved in the darkening reaction mixture, stirring was continued an additional 2 minutes. The homogeneous reaction mixture was then rapidly cooled to room temperature with an ice/water bath. The reaction mixture was concentrated via rotary evaporator using pump vacuum and a water bath temperature of 45° C. The residue was taken up in 2 L of CH₂ Cl₂ and slowly poured into a stirring mixture of 2 L CH₂ Cl₂ and 6 L of H₂ O chilled to 10° C. The layers were separated and enough 50percent NaOH was added to the aqueous phase to give a pH of 2-4. The aqueous phase was extracted with additional CH₂ Cl₂ (2*2 L). The combined organic layers were washed with 4 L of H₂ O and dried (MgSO₄). The solution was vacuum filtered through 1 kg of silica gel. The silica gel was washed with 4 L of ethyl acetate/hexanes (1:1). The filtrate was concentrated in vacuo to afford 564 g (78percent yield) of 3-chloro-5-methoxypyridazine as a pale yellow solid. The product was stored in a freezer to prevent gradual decomposition. The product was recrystallized from ethyl acetate/cyclohexane to give a white solid, mp=98°-100° C. Anal. Calc. for C₅ H₅ N₂ OCl: C, 4.154; H, 3.49; N, 19.38 Found: C, 41.62; H, 3.51; N, 19.34

Reference： [1] Patent: US5536701, 1996, A,
[2] Patent: US5616789, 1997, A,
[3] Patent: US5559080, 1996, A,

5
[ 124-41-4 ]
[ 1837-55-4 ]
[ 123696-02-6 ]

Reference： [1] Patent: WO2012/114268, 2012, A1, . Location in patent: Page/Page column 119

6
[ 63910-43-0 ]
[ 123696-02-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4716 - 4730
[2] Monatshefte fuer Chemie, 1989, vol. 120, p. 329 - 342

7
[ 67-56-1 ]
[ 124-41-4 ]
[ 1837-55-4 ]
[ 123696-02-6 ]

Reference： [1] Patent: US2014/73651, 2014, A1, . Location in patent: Paragraph 0875; 0876

8
[ 173206-12-7 ]
[ 123696-02-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1473 - 1476

9
[ 173206-14-9 ]
[ 123696-02-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 5, p. 1473 - 1476

10
[ 152732-22-4 ]
[ 123696-02-6 ]

Reference： [1] Patent: WO2017/102091, 2017, A1,

[ 123696-02-6 ] Synthesis Path-Downstream 1~35

1
[ 123696-01-5 ]
[ 123696-02-6 ]

Yield	Reaction Conditions	Operation in experiment
45%	With trichlorophosphate; at 1100.0℃; for 0.166667h;	A suspension of <strong>[123696-01-5]5-methoxypyridazin-3(2H)-one</strong> (250 mg, 1.98 mmol) in phosphorus oxychloride (1.5 mL, 16 mmol) was stirred at 100C for 10 minutes. The reaction mixture was poured into ice water and sodium carbonate was added until a basic pH-was reached. The mixture was extracted with diethyl ether, the organic phase was dried (magnesium sulfate), filtered and the solvent was removed in vacuum. The residue was crystallized from 1,2-dichloroethane to give 130 mg (45 % yield) of the title compound. LC-MS (Method 5): R = 0.85 mm; MS (ESIpos): m/z = 145 [M+H] 1H-NMR (400 MHz, DMSO-d6) [ppm]: 2.495 (0.78), 2.499 (1.07), 2.503 (0.84), 3.317 (11.94),3.944 (16.00), 7.528 (2.28), 7.534 (2.29), 8.988 (2.34), 8.994 (2.34).

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1473 - 1476
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 4716 - 4730
[3]Monatshefte fur Chemie,1989,vol. 120,p. 329 - 342
[4]Patent: WO2017/102091,2017,A1 .Location in patent: Page/Page column 455; 456

2
[ 67-56-1 ]
[ 123696-02-6 ]
[ 2096-20-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1473 - 1476

3
[ 123696-02-6 ]
[ 20733-11-3 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4716 - 4730

4
[ 123324-71-0 ]
[ 123696-02-6 ]
[ 943997-55-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3497 - 3514

5
[ 123696-02-6 ]
[ 748142-02-1 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4716 - 4730

6
[ 123696-02-6 ]
[ 748142-03-2 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4716 - 4730

7
[ 63910-43-0 ]
[ 123696-02-6 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4716 - 4730
[2]Monatshefte fur Chemie,1989,vol. 120,p. 329 - 342

8
[ 173206-14-9 ]
[ 123696-02-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1473 - 1476

9
[ 173206-12-7 ]
[ 123696-02-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1473 - 1476

10
[ 64-17-5 ]
[ 201230-82-2 ]
[ 123696-02-6 ]
[ 627525-71-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In ethanol; at 120.0℃; under 30003.0 Torr; for 5.0h;	3-Chloro-5-methoxy-pyridazine (Bryant, R. D.; Kunng, F.-A.; South, M. S. J. Heterocycl. Chem. (1995), 32(5), 1473-6.) (21 g, 0.145 mol), bis(triphenylphosphine)palladium dichloride (10.2 g, 14.5 mmol) and triethylamine (30.5 ml, 0.218 mol) in ethanol (420 ml) were heated at 120 C. under a 40 bar pressure of carbon monoxide for 5 hours. The reaction mixture was cooled, filtered and concentrated in vacuo. The residue was taken in CH2Cl2 (200 ml), washed with H2O (twice), dried over Na2SO4 and concentrated in vacuo. The crude solid was stirred in Et2O and filtered to provide 22.1 g of a light brown solid which was chromatographed over silica gel (hexane - ethylacetate 99 : 1 to 50 : 50) to provide 5-methoxy-pyridazine-3-carboxylic acid ethyl ester (21.1 g, 80%) as a pale yellow solid, MS: m/e=183.2 (M+H+).

Reference： [1]Patent: US2003/229096,2003,A1 .Location in patent: Page 16; 6

11
[ 123696-02-6 ]
[ 144432-85-9 ]
[ 627525-81-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tri-tert-butyl phosphine; caesium carbonate;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; In 1,4-dioxane; at 90.0℃; for 22.0h;	3-Chloro-5-methoxy-pyridazine (Bryant, R. D.; Kunng, F.-A.; South, M. S. J. Heterocycl. Chem. (1995), 32(5), 1473-6.) (300 mg, 2.08 mmol), <strong>[144432-85-9]3-chloro-4-fluorophenylboronic acid</strong> (724 mg, 4.15 mmol), Cs2CO3 (2 g, 6.2 mmol) and tris(dibenzylideneacetone)dipalladium chloroform complex (96.7 mg, 0.093 mmol) were mixed and a solution of tri-tert-butylphosphine (45.4 mg, 0.22 mmol) in degassed dioxane (6 ml) was added. The mixture was heated at 90C. for 22 hours then cooled to room temperature, ethylacetate was added, the solid was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed over silica gel (hexane-ethyl acetate 4:1) to provide 3-(3-chloro-4-fluoro-phenyl)-5-methoxy-pyridazine (330 mg, 67%) as an orange solid, MS: m/e=239.3 (M+H+).

Reference： [1]Patent: US2003/229096,2003,A1 .Location in patent: Page 17

12
3,5-difluoro-4-trimethylstannylpyridine [ No CAS ]
[ 123696-02-6 ]
[ 660425-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 80.0℃; for 16.0h;	A degassed solution of <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (473 mg, 3.27 mmol), 3,5-difluoro-4-trimethylstannanylpyridine (1.0 g, 3.6 mmol), copper [(I)] iodide (31 mg, 0.2 mmol) and lithium chloride (416 mg, 9.8 mmol) was formed in 1,4-dioxane (10 ml). Tetrakis (triphenylphosphine)- palladium [(0)] (100 mg) was added and the mixture heated to [80C] for 16 h. The solvent was removed and the residue was purified by flash column chromatography over silica using 40% isohexane: 60% ethyl acetate to give 3- (3, 5-difluoropyridin-4-yl)-5-methoxypyridazine as a pale yellow solid (220 mg): 8H (400 MHz, [CDCL3)] 7.10-7. 12 [(1H,] m), 8. 54 (2H, s), 9.02 [(1H,] d, [J 3.] 1); [7NLZ] (ES+) 224.

Reference： [1]Patent: WO2004/14865,2004,A1 .Location in patent: Page 84-85

13
[ 128796-39-4 ]
[ 123696-02-6 ]
[ 849680-80-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90.0℃; for 18.0h;	Example 11; (A) 5-Methoxy-3-(4-trifluoromethyl) phenyl) PYRIDAZINE. A mixture of 3-chloro-5- METHOXYPYRIDAZINE (0. 146 mg, 1 MMOL, (synthesized according to the method of Bryant, R. D. ; Kunng, F-A. and South, M. S. J. Heterocyclic Chem. 1995, 32, 1473.), 4-(TRIFLUOROMETHYL) PHENYLBORONIC acid (285 mg, 1. 5 MMOL, Aldrich) in ethylene glycol dimethyl ether (2. 0 ML) was DEGASSED by bubbling nitrogen through the solution for 15 min. 1. 5 ML of 2N potassium carbonate and tetrakis (TRIPHENYLPHOSPHINE) palladium (0) (185 mg, 0. 16 MMOL, Strem) were added and the mixture was heated at 90 C for 18 H. The reaction mixture was cooled to room temperature and filtered through A pad of Celte. The resulting crude product was purified by PREPARATIVE HPLC (1-99% CH3CN/H2O modified with 0. 1 % TFA) to give 5-METHOXY-3- (4- (TRIFLUOROMETHYL) phenyl) pyridazin as A tan solid [MS (ESI, pos. ion) m/z : 255 (M+1)].

Reference： [1]Patent: WO2005/33105,2005,A2 .Location in patent: Page/Page column 95

14
[ 108-48-5 ]
[ 123696-02-6 ]
3-[[4-chloro-1-methyl-5-(methylthio)-1H-pyrazol-3-yl]oxy]-5-methoxypyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	In toluene;	EXAMPLE 6 This example describes the preparation of 3-[[4-chloro-1-methyl-5-(methylthio)-1H-pyrazol-3-yl]oxy]-5-methoxypyridazine (Compound No. 28). 4-Chloro-1-methyl-5-(methylthio)-1H-pyrazol-3-ol which is a known compound (2.7 g, 0.015 mole), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (1.45 g, 0.01 mole), and 2,6-lutidine (1.4 mL, 0.012 moles) were heated to reflux in toluene (40 mL) under N2 for 18 h. The mixture was then poured into aqueous ammonium chloride and extracted 3*100 mL with ethyl acetate. The organic layers were washed with water and brine, dried (MgSO4), filtered and evaporated in vacuo. The crude solid was purified by flash chromatography to give 3-[[4-chloro-1-methyl-5-(methylthio)-1H-pyrazol-3-yl]oxy]-5-methoxypyridazine (1.1 g, 26% yield) as a white solid.

Reference： [1]Patent: US5536701,1996,A

15
[ 108-48-5 ]
[ 132631-85-7 ]
[ 123696-02-6 ]
5-methoxy-3-[[1-methyl-3-(pentafluoroethyl)-1H-pyrazol-5-yl]oxy]pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	In toluene;	B. 1-Methyl-3-(pentafluoroethyl)-1H-pyrazol-5-ol (0.44 g, 0.002 mole), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (0.29 g, 0.002 mole), and 2,6-lutidine (0.27 g, 0.0024 mole) were refluxed under N2 in toluene (8 mL) for 15 h. This mixture was poured into ethyl acetate and washed with 7% HCl, water and then with saturated sodium bicarbonate. The organic layer was dried (MgSO4), filtered through silica gel with ethyl acetate, and evaporated in vacuo to give 5-methoxy-3-[[1-methyl-3-(pentafluoroethyl)-1H-pyrazol-5-yl]oxy]pyridazine as a light yellow solid. The compound was recrystallized to give (0.45 g, 69% yield) Compound 18, a white solid.

Reference： [1]Patent: US5536701,1996,A

16
[ 108-48-5 ]
5-hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxaldehyde [ No CAS ]
[ 123696-02-6 ]
5-[(5-methoxy-3-pyridazinyl)oxy]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In ethyl acetate; toluene;	B. 5-Hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxaldehyde (3.0 g, 0.015 mole), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (2.3 g, 0.015 mole), 2,6-lutidine (2.8 g, 0.025 mole), and toluene (80 mL) were heated in a flask equipped with a short Vigreux column until 5 mL of solvent had distilled. The mixture was then held at reflux for 4 hours, cooled, poured into 1% hydrochloric acid, and extracted with a mixture of ether and ethyl acetate. The combined extracts were washed with 1% hydrochloric acid, 1% sodium hydroxide, 5% sodium chloride, then dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography using ethyl acetate/cyclohexane to give 5-[(5-methoxy-3-pyridazinyl)oxy]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxaldehyde (2.53 g, 55% yield) as a yellow solid.

Reference： [1]Patent: US5536701,1996,A

17
[ 108-48-5 ]
3-[(1,1-dimethylethyl)dimethylsilyl]-1-methyl-1H-pyrazol-5-ol [ No CAS ]
[ 123696-02-6 ]
3-[[3-[(1,1-dimethylethyl)dimethylsilyl]-1-methyl-1H-pyrazol-5-yl]oxy]-5-methoxypyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	In 5,5-dimethyl-1,3-cyclohexadiene;	C. 3-[(1,1-Dimethylethyl)dimethylsilyl]-1-methyl-1H-pyrazol-5-ol (0.48 g, 0.0023 mole), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (0.36 g, 0.00249 mole) and 2,6-lutidine (0.396 mL, 0.003396 moles) were refluxed under N2 in xylene (20 mL) for 18 hours. The mixture was then filtered through silica gel with ethyl acetate and evaporated in vacuo. The crude compound was purified by reverse phase chromatography to give 3-[[3-[(1,1-dimethylethyl)dimethylsilyl]-1-methyl-1H-pyrazol-5-yl]oxy]-5-methoxypyridazine (0.19 g, 26% yield) as a brown solid.

Reference： [1]Patent: US5536701,1996,A

18
3-hydroxy-5-methoxypyridazine [ No CAS ]
[ 7732-18-5 ]
[ 123696-02-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide; trichlorophosphate; In hexane; dichloromethane; ethyl acetate;	E. 3-Hydroxy-5-methoxypyridazine (629.6 g, 4.99 moles) and phosphorus oxychloride (2.5 L, 27 moles) were added to a 5 L round bottomed flask equipped with a heating mantle and a mechanical stirrer. The resulting stirred slurry was rapidly heated (<30 min) to 75 C. At this temperature the heating mantle was removed. The reaction mixture continued to exotherm to a final temperature of 82.3 C. After the solids had dissolved in the darkening reaction mixture, stirring was continued an additional 2 minutes. The homogeneous reaction mixture was then rapidly cooled to room temperature with an ice/water bath. The reaction mixture was concentrated via rotary evaporator using pump vacuum and a water bath temperature of 45 C. The residue was taken up in 2 L of CH2 Cl2 and slowly poured into a stirring mixture of 2 L CH2 Cl2 and 6 L of H2 O chilled to 10 C. The layers were separated and enough 50% NaOH was added to the aqueous phase to give a pH of 2-4. The aqueous phase was extracted with additional CH2 Cl2 (2*2 L). The combined organic layers were washed with 4 L of H2 O and dried (MgSO4). The solution was vacuum filtered through 1 kg of silica gel. The silica gel was washed with 4 L of ethyl acetate/hexane (1:1). The filtrate was concentrated in vacuo to afford 564 g (78% yield) of 3-chloro-5-methoxypyridazine as a pale yellow solid. The product was stored in a freezer to prevent gradual decomposition. The product was recrystallized from ethyl acetate/cyclohexane to give a white solid, mp=98-100 C. Anal. Calc. for C5 H5 N2 OCl: C, 41.54; H, 3.49; N, 19.38 Found: C, 41.62; H, 3.51; N, 19.34
78%	With sodium hydroxide; trichlorophosphate; In dichloromethane; ethyl acetate;	E. 3-Hydroxy-5-methoxypyridazine (629.6 g, 4.99 moles) and phosphorous oxychloride (2.5 L, 27 moles) were added to a 5 L round bottomed flask equipped with a heating mantle and a mechanical stirrer. The resulting stirred slurry was rapidly heated (<30 min) to 75 C. At this temperature the heating mantle was removed. The reaction mixture continued to exotherm to a final temperature of 82.3 C. After the solids had dissolved in the darkening reaction mixture, stirring was continued an additional 2 minutes. The homogeneous reaction mixture was then rapidly cooled to room temperature with an ice/water bath. The reaction mixture was concentrated via rotary evaporator using pump vacuum and a water bath temperature of 45 C. The residue was taken up in 2 L of CH2 Cl2 and slowly poured into a stirring mixture of 2 L CH2 Cl2 and 6 L of H2 O chilled to 10 C. The layers were separated and enough 50% NaOH was added to the aqueous phase to give a pH of 2-4. The aqueous phase was extracted with additional CH2 Cl2 (2*2 L). The combined organic layers were washed with 4 L of H2 O and dried (MgSO4). The solution was vacuum filtered through 1 kg of silica gel. The silica gel was washed with 4 L of ethyl acetate/hexanes (1:1). The filtrate was concentrated in vacuo to afford 564 g (78% yield) of 3-chloro-5-methoxypyridazine as a pale yellow solid. The product was stored in a freezer to prevent gradual decomposition. The product was recrystallized from ethyl acetate/cyclohexane to give a white solid, mp=98-100 C. Anal. Calc. for C5 H5 N2 OCl: C, 4.154; H, 3.49; N, 19.38 Found: C, 41.62; H, 3.51; N, 19.34
	With sodium hydroxide; trichlorophosphate; In dichloromethane; ethyl acetate;	Anal. Calc. for C5 H6 N2 O2: C, 47.62; H, 4.80;N, 22.21 Found: C, 47.60; H, 4.83;N, 22.18 E. 3-Hydroxy-5-methoxypyridazine (629.6 g, 4.99 moles) and phosphorus oxychloride (2.5 L, 27 moles) were added to a 5 L round bottomed flask equipped with a heating mantle and a mechanical stirrer. The resulting stirred slurry was rapidly heated (<30 min) to 75 C. At this temperature the heating mantle was removed. The reaction mixture continued to exotherm to a final temperature of 82.3 C. After the solids had dissolved in the darkening reaction mixture, stirring was continued an additional 2 minutes. The homogeneous reaction mixture was then rapidly cooled to room temperature with an ice/water bath. The reaction mixture was concentrated via rotary evaporator using pump vacuum and a water bath temperature of 45 C. The residue was taken up in 2 L of CH2 Cl2 and slowly poured into a stirring mixture of 2 L CH2 Cl2 and 6 L of H2 O chilled to 10 C. The layers were separated and enough 50% NaOH was added to the aqueous phase to give a pH of 2-4. The aqueous phase was extracted with additional CH2 Cl2 (2*2 L). The combined organic layers were washed with 4 L of H2 O and dried (MgSO4). The solution was vacuum filtered through 1 kg of silica gel. The silica gel was washed with 4 L of ethyl acetate/hexanes (1:1). The filtrate was concentrated in-vacuo to afford 564 g (78% yield) of 3-chloro-5-methoxypyridazine as a pale yellow solid. The product was stored in a freezer to minimize decomposition. The product was recrystallized from ethyl acetate/cyclohexane to give a white solid, mp=98 C.-100 C. Anal. Calc. for C5 H5 N2 OCl: C, 41.54; H, 3.49;N, 19.38 Found: C, 41.62; H, 3.51;N, 19.34

Reference： [1]Patent: US5536701,1996,A
[2]Patent: US5616789,1997,A
[3]Patent: US5559080,1996,A

19
2,6-1-lutidine [ No CAS ]
[ 122431-37-2 ]
[ 123696-02-6 ]
5-methoxy-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5yl-]oxy]pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; sodium hydroxide; In toluene;	EXAMPLE 7 This example describes the preparation of 5-methoxy-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5yl-]oxy]pyridazine (Compound No. 5). 1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol (4.0 g, 0.024 mole), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (3.5 g, 0.024 mole), and 2,6-1-lutidine (3.0 g, 0.028 mole) were heated to reflux in toluene (75 mL) under N2 and held there for 22.5 h. The mixture was poured into diluted HCl (1%) aqueous solution and extracted 2100 mL with ethyl acetate. The organic layer was extracted with brine followed by dilute NaOH (1%, 2100 mL). The organic layer was dried (MgSO4), filtered through silica gel with ethyl acetate and evaporated in vacuo to give 5-methoxy-3-[[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy]-pyridazine (6.25 g, 95% yield) as a light brown solid. This solid was recrystallized from ethyl acetate/cyclohexane.

Reference： [1]Patent: US5536701,1996,A

20
5-ethoxy-2,4-dihydro-2-methyl-3H-pyrazol-3-one [ No CAS ]
[ 123696-02-6 ]
3-[(3-ethoxy-1-methyl-1H-pyrazol-5-yl)oxy]-5-methoxypyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With hydrogenchloride; potassium carbonate; dimethyl sulfoxide; copper(I) bromide; In cyclohexane; ethyl acetate;	B. 5-Ethoxy-2,4-dihydro-2-methyl-3H-pyrazol-3-one (0.63 g, 0.0044 mole), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (0.64 g, 0.0044 mole), potassium carbonate (1.50 g, 0.010 mole), cuprous bromide (0.05 g, 0.0003 mole) and anhydrous dimethyl sulfoxide (10 mL) were heated and held at 90 C. for 42 hours. The mixture was cooled, treated with 1% hydrochloric acid solution and extracted with ethyl acetate. The combined extracts were washed with 2% sodium hydroxide, dried with magnesium sulfate, filtered and concentrated in vacuo. Purification by chromatography on silica gel using ethyl acetate/cyclohexane gave a tan solid, which was recrystallized from ethyl acetate/methylcyclohexane to give 5-methoxy-3-[(3-ethoxy-1-methyl-1H-pyrazol-5-yl)oxy]pyridazine (0.22 g, 22% yield) as a white solid.

Reference： [1]Patent: US5536701,1996,A

21
[ 124-41-4 ]
[ 1837-55-4 ]
[ 123696-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 90.0℃; for 1.0h;	Example 131 2-Chloro-N-(1 -hydroxy-cyclohexylmethyl)-5-(5-methoxy-pyridazin-3- yloxy)-benzamide131.1 3-chloro-5-methoxyDyridazineTo a solution of <strong>[1837-55-4]3,5-dichloropyridazine</strong> (300 mg) in MeOH (2 mL) was added a 5.4 M solution of sodium methoxide in MeOH (0.410 mL) and the reaction mixture was stirred for 1 h at 90C. It was quenched with H20 and extracted with EtOAc. The organic phase was washed with a 5% solution of KHS04, a sat. solution of NaHC03 and brine, dried over MgS04 and concentrated in vacuo to give the crude titled compound as an orange solid.1H NMR ((CD3)2SO) delta: 9.01 (d, J = 2.4 Hz, 1 H), 7.55 (d, J = 2.4 Hz, 1 H), 3.96 (s, 3 H)

Reference： [1]Patent: WO2012/114268,2012,A1 .Location in patent: Page/Page column 119

22
[ 67-56-1 ]
[ 124-41-4 ]
[ 1837-55-4 ]
[ 123696-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 90.0℃; for 1.0h;	131.1 3-chloro-5-methoxypyridazine To a solution of <strong>[1837-55-4]3,5-dichloropyridazine</strong> (300 mg) in MeOH (2 mL) was added a 5.4 M solution of sodium methoxide in MeOH (0.410 mL) and the reaction mixture was stirred for 1 h at 90 C. It was quenched with H2O and extracted with EtOAc. The organic phase was washed with a 5% solution of KHSO4, a sat. solution of NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to give the crude titled compound as an orange solid. 1H NMR ((CD3)2SO) delta: 9.01 (d, J=2.4 Hz, 1H), 7.55 (d, J=2.4 Hz, 1H), 3.96 (s, 3H)

Reference： [1]Patent: US2014/73651,2014,A1 .Location in patent: Paragraph 0875; 0876

23
[ 1071539-89-3 ]
[ 123696-02-6 ]
[ 1071535-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 100.0℃; for 4.0h;Inert atmosphere; Sealed tube;	Example 397 Synthesis of 5-Methoxy-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)pyridazin-3-amine A pyrex reaction tube was charged with potassium phosphate (88 mg, 415 mumol), Pd2 dba3 (16 mg, 17 mmol), Xantphos (22 mg, 38 mmol), 4-(7-methoxy-1,5-naphthyridin-4-yloxy)benzenamine (92 mg, 346 mumol), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (50 mg, 346 mol), and toluene (1 mL). The tube was purged with argon, sealed, and the mixture was heated at 100 C. for 4 h. LCMS showed complete conversion to desired product. The mixture was then concentrated and purified by silica gel chromatography using 0 to 60% (90/10/1 DCM/MeOH/ammonium hydroxide) in DCM. MS: M+H+=376.

Reference： [1]Patent: US2014/336182,2014,A1 .Location in patent: Paragraph 0575

24
(R)-(3-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)phenyl)boronic acid [ No CAS ]
[ 123696-02-6 ]
6-((R)-5-{2-[3-(5-methoxypyridazin-3-yl)benzylamino]ethyl}-2-oxo-oxazolidin-3-yl)-4H-benzo[1,4]thiazin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%		General procedure: A suspension of 4-bromo-2-methoxybenzamide (48 mg; commercial) and the compound of Preparation W (60 mg) in toluene/EtOH (0.4 mL; 4: 1) was treated with sat. aq. Na2C03 (0.4 mL) and degassed by bubbling with nitrogen for 5 min. The suspension was treated with Pd(PPh3)4 (4 mg) and refluxed overnight in a sealed tube. The reaction mixture was allowed to reach rt and diluted with water and EA. The aq. layer was extracted with EA and the combined org. layers were washed with brine, dried over MgS04, filtered, evaporated under reduced pressure and purified by prep-HPLC (Method 2), affording a colourless foam (10 mg; 22% yieldStarting from <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (46 mg; commercial) and the compound of Preparation W (76 mg) and proceeding in analogy to Example 29, the title compound was obtained, after purification by prep-HPLC (Method 2), as a colourless foam (6 mg; 11% yield). MS I (ESI, m/z): 492.1 [M+H+]; tR = 0.60 min.

Reference： [1]Patent: WO2014/170821,2014,A1 .Location in patent: Page/Page column 128; 129

25
[ 916326-10-8 ]
[ 123696-02-6 ]
ethyl 5-(5-methoxypyridazin-3-yl)nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 85.0℃;Inert atmosphere; Sealed tube;	<strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (149 mg; commercial), 3-(ethoxycarbonyl)pyridine- 5-boronic acid pinacol ester (289 mg; commercial), K2C03 (276 mg) and Pd(PPh3)4 (173 mg) were suspended in DMF (3.4 mL). The sealed tube was evacuated and refilled with N2 three times. The mixture was then stirred overnight at 85C. The reaction mixture was cooled down to rt and diluted with EA and water. The layers were separated and the aq. phase was extracted twice with EA. The combined org. layers were dried over MgS04 and concentrated under reduced pressure. The crude was purified by prep-HPLC (Method 6) to afford the desired product as a white solid (156 mg; 60% yield). MSI (ESI, m/z): 260.2 [M+H+]; tR = 0.72 min.

Reference： [1]Patent: WO2014/170821,2014,A1 .Location in patent: Page/Page column 118

26
[ 123696-02-6 ]
(4-(5-methoxypyridazin-3-yl)pyridin-2-yl)methanol [ No CAS ]

Reference： [1]Patent: WO2014/170821,2014,A1

27
[ 123696-02-6 ]
4-(5-methoxypyridazin-3-yl)picolinaldehyde [ No CAS ]

Reference： [1]Patent: WO2014/170821,2014,A1

28
[ 957062-72-5 ]
[ 123696-02-6 ]
methyl 4-(5-methoxypyridazin-3-yl)picolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 85.0℃;Inert atmosphere; Sealed tube;	<strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (253 mg; commercial), methyl 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)picolinate (447 mg; commercial), K2C03 (470 mg) and tetrakis(triphenylphosphine)palladium (295 mg) were suspended in DMF (5.78 mL). The sealed tube was evacuated and refilled with N2 three times. The mixture was then heated to 85C and stirred at this temperature overnight. The reaction mixture was cooled to rt and partitionned between EA/MeOH 9: 1 and diluted with sat. aq. H4OH. The two phases were separated and org. layer was washed twice with EA/MeOH 9: 1 and with sat. aq. NaHC03, dried over MgS04 and concentrated. The aq. phases were combined and concentrated. The residue was purified by prep-HPLC (Method 7). The residue (from aq. phases) was triturated with DCM/MeOH 4: 1, the solid (salt) was filtered, washed with DCM/MeOH 4: 1 and the filtrate was concentrated. The residue was purified by prep-HPLC (Method 7) and a pink solid (87 mg; 22% yield) was obtained. MSI (ESI, m/z): 247.07 [M+H+]; tR = 0.60 min.

Reference： [1]Patent: WO2014/170821,2014,A1 .Location in patent: Page/Page column 118; 119

29
8,8-difluoro-3-(2-oxo-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-diazaspiro[4.5]decane-2,4-dione [ No CAS ]
[ 123696-02-6 ]
C₂₁H₂₀F₂N₄O₄ [ No CAS ]

Reference： [1]Patent: WO2015/136947,2015,A1 .Location in patent: Paragraph 0435; 0437

30
[ 152732-22-4 ]
[ 123696-02-6 ]

Reference： [1]Patent: WO2017/102091,2017,A1

31
C₂₀H₂₃BO₄ [ No CAS ]
[ 123696-02-6 ]
2-(benzyloxy)-3-(5-methoxypyridazin-3-yl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.6%	With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); caesium carbonate; XPhos; In 1,2-dimethoxyethane; water; at 60.0℃; for 24.0h;Inert atmosphere;	A mixture of 2-(benzyloxy)-3-(4,4,5,5-tetramethyl-1 ,3-dioxolan-2-yl)benzaldehyde (250 mg, 0.74 mmol)(prepared as in the method described for the intermediate in example 18b starting from 18a), <strong>[123696-02-6]3-chloro-5-methoxypyridazine</strong> (0.09 mL, 0.74 mmol), (XPhos)(35.24 mg, 0.07 mmol), XPhos Pd G2 (58.3 mg, 0.07 mmol) and CsCOs (722 mg, 2.22 mmol) in a mixture of monoglyme (2.4 mL) and H2O (0.4 mL)(deoxygenated by bubbling N2 through) was stirred at 60 C for 24 h. The mixture was allowed to cool, diluted with EtOAc (10 mL) and washed with H2O (4 mL). The organic phase was dried (MgSCU) and the resultant material purified by silica gel chromatography using 40 -100% EtOAc in petroleum ether to afford 2-benzyloxy-3-(5-methoxypyridazin-3-yl)benzaldehyde (134 mg, 56.6 % ). LC-MS (Method A) 321.0 [M+H]+; RT 2.51 min. 1 H NMR (Method C) (CDC ): delta ppm 10.37 (d, J = 0.8 Hz, 1 H), 8.90 (d, J = 3.0 Hz, 1 H), 8.21 (dd, J = 7.6, 1.9 Hz, 1 H), 7.98 (dd, J = 7.7, 1.9 Hz, 1 H), 7.50 - 7.39 (m, 2H), 7.34 - 7.27 (m, 3H), 7.16 - 7.10 (m, 2H), 4.75 (s, 2H), 3.73 (s, 3H).

Reference： [1]Patent: WO2017/137744,2017,A1 .Location in patent: Page/Page column 188

32
[ 5049-61-6 ]
[ 123696-02-6 ]
C₉H₉N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃; for 40.0h;Inert atmosphere;	Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 3- chloro-5-methoxypyridazine (2) (289mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13ml_). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt. EtOAc (15ml_), H20 (10mL) and brine (5mL) were added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with EtOAc (15ml_). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (24mg, 6%).

Reference： [1]Patent: WO2019/166824,2019,A1 .Location in patent: Page/Page column 120; 121

33
[ 123696-02-6 ]
5-methoxy-N-(pyrazin-2-yl)-N-({5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophen-2-yl}methyl)pyridazin-3-amine [ No CAS ]

Reference： [1]Patent: WO2019/166824,2019,A1

34
[ 123696-02-6 ]
[ 1066-54-2 ]
5-methoxy-3-[2-(trimethylsilyl)ethynyl]pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20.0℃; for 1.0h;	To a solution of 5-amino-3-({l-[(lR,2R)-4-ethynyl-4-fluoro-2-phenylcyclohexane carbonyl]-4-hydroxypiperidin-4-yl}methyl)-6-(4-fluorophenoxy)-3,4-dihydropyrimidin-4- one (110 mg, 0.2 mmol, 1.0 eq.) in THF (2 mL) was added copper(I) iodide (33 mg, 0.02 mmol, 0.08 eq.) and bis(triphenylphosphine)palladium(II) dichloride (5.5 mg, 0.01 mmol, 0.04 eq.). The reaction mixture was degassed under nitrogen for 5 minutes before adding triethylamine (0.04 mL, 0.29 mmol, 1.5 eq.) followed by iodobenzene (0.03 mL, 0.29 mmol, 1.5 eq.). The reaction mixture was stirred at r.t. for 1 hour. The mixture was partitioned between EtOAc (20 mL) and brine (20 mL). The organic layer was separated, dried (MgS04) and evaporated in vacuo to afford a crude brown oil. The residue was purified via flash chromatography using DCM-4.5 % MeOH/DCM (gradient) as eluent to give: First elute: EXAMPLE 135 obtained as a yellow oil. LC/MS (Method B): RT = 1.22; m/z = 639 [M+H]+ 1H NMR (399 MHz, DMSO- ) d 7.66-7.41 (m, 6H), 7.34-7.18 (m, 7H), 7.11-7.07 (m, 2H) 4.94-4.49 (m, 3H), 4.05-3.53 (m, 4H), 3.17 (m, 2H), 2.70 (s, 1H), 2.39-1.99 (m, 4H), 1.86 (d, J= 9.1 Hz, 2H), 1.52-1.02 (m, 3H), 0.77 (dt, J= 12.7, 6.2 Hz, 1H), 0.66-0.41 (m, 1H). Second elute: EXAMPLE 136 obtained as a brown oil. LC/MS (Method B): RT = 1.22; m/z = 619 [M-HF]+ 1H NMR (399 MHz, DMSO- ) d d 7.66-7.40 (m, 6H), 7.33-7.17 (m, 7H), 7.12-7.08 (m, 2H), 4.77 (dd, J = 49.4, 5.7 Hz, 3H), 4.11-3.53 (m, 4H), 3.18 (dt, j = 27.8, 11.8 Hz, 2H), 2.99-2.59 (m, 1H), 2.41-1.93 (m, 4H), 1.74 (dt, j= 51.7, 12.9 Hz, 2H), 1.50-1.01 (m, 3H), 0.92-0.48 (m, 2H).

Reference： [1]Patent: WO2020/8013,2020,A1 .Location in patent: Page/Page column 163; 204; 205

35
[ 123696-02-6 ]
3-ethynyl-5-methoxypyridazine [ No CAS ]

Reference： [1]Patent: WO2020/8013,2020,A1

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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 123696-02-6 ]

Quality Control of [ 123696-02-6 ]

Related Doc. of [ 123696-02-6 ]

Product Details of [ 123696-02-6 ]

Calculated chemistry of [ 123696-02-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 123696-02-6 ]

Application In Synthesis of [ 123696-02-6 ]

[ 123696-02-6 ] Synthesis Path-Upstream 1~10

[ 123696-02-6 ] Synthesis Path-Downstream 1~35

Related Functional Groups of [ 123696-02-6 ]

Chlorides

Ethers

Related Parent Nucleus of [ 123696-02-6 ]

Pyridazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 123696-02-6 ]

Related Parent Nucleus of
[ 123696-02-6 ]